Tributylphosphine → HCID 86583975, compound

HRID 1270052Notes

Reaction equation

[C:1]1([C:7]#[C:8]/[CH:9]=[CH:10]/[CH2:11][OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(P(CCCC)CCCC)CCC.[CH2:26]([O:28][C:29](=[O:42])[C@@H:30]([O:39][CH2:40][CH3:41])[CH2:31][C:32]1[CH:37]=[CH:36][C:35](O)=[CH:34][CH:33]=1)[CH3:27].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1C=CC=CC=1>[CH2:26]([O:28][C:29](=[O:42])[C@@H:30]([O:39][CH2:40][CH3:41])[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:12][CH2:11]/[CH:10]=[CH:9]/[C:8]#[C:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:34][CH:33]=1)[CH3:27]

Participants

Conditions

Temperature: 0 °C

Procedure

(E)-5-Phenyl-pent-2-en-4-yn-1-ol (328 mg, 2.07 mmol), tributylphosphine (606 mg, 3.0 mmol) and (S)-2-ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (Tetrahedron Letters, Vol. 35, No. 19, 3139–3142, 1994) (495 mg, 2.07 mmol) were successively dissolved in dry benzene (30 mL) under a nitrogen atmosphere and the solution cooled to 0° C. Solid 1,1′-(azodicarbonyl) dipiperidine (756 mg, 3.0 mmol) was added, the mixture stirred for 10 min., then warmed to room temperature and stirred for 16 h. The reaction mixture was filtered and the filtrate concentrated in vacuo. The product was purified by flash column chromatography eluting with toluene graduated to toluene/ethyl acetate (19:1) to give 450 mg (57%) of the title compound.

Workup

temperaturewarmed to room temperature
stirringstirred for 16 h
filtrationThe reaction mixture was filtered
concentrationthe filtrate concentrated in vacuo
customThe product was purified by flash column chromatography
washeluting with toluene

Sources & evidence

ORD record: ord-5f93332082814bc89b8aee7a26890030
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07202213B2

Reaction notes

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